A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Windsor vacation rentals

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

1. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
$822 nightly
The price is $932
Nov 10 - Nov 11
Total with taxes and fees
Sauna, Cold Plunge & Fire Pit Near Wineries
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

2. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
$842 nightly
The price is $955
Nov 10 - Nov 11
Total with taxes and fees
Elegant Vineyard Living at a Private Wine Country Estate
A house with a swimming pool, outdoor furniture, and a well-maintained garden.

3. Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (5 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
$1,628 nightly
The price is $1,826
Nov 12 - Nov 13
Total with taxes and fees
Eastside Eden - Pool, Hot Tub and Tastings Included
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

4. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (19 reviews)
"Great place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
$337 nightly
The price is $375
Dec 1 - Dec 2
Total with taxes and fees
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

5. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (139 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
$103 nightly
The price is $117
Dec 10 - Dec 11
Total with taxes and fees
Wildhaven Sonoma Glamping
Private kitchen

6. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
$297 nightly
The price is $337
Nov 10 - Nov 11
Total with taxes and fees
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A hallway with white paneling and wooden doors, leading to an outdoor area with greenery.

7. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
9.8 out of 10, Exceptional, (22 reviews)
"Nice clean relaxing place to stay near the river! Was perfect for our little weekend getaway."
United States
Greg K.
$366 nightly
The price is $414
Nov 10 - Nov 11
Total with taxes and fees
2BR Bungalow - Russian River & Wine Country
A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

8. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (44 reviews)
"We had a great stay. The house was clean, the beds were comfy and a very convenient location. Just wish there was an ironing board. I would definitely recommend staying here."
United States
Patricia A.
$454 nightly
The price is $506
Nov 12 - Nov 13
Total with taxes and fees
Serenity at the Russian River
A deck with outdoor seating, a grill, and a view of a house with large windows.

9. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (38 reviews)
"Great stay, highly recommend!"
United States
Jana P.
$432 nightly
The price is $481
Nov 18 - Nov 19
Total with taxes and fees
Somms Rest ⎮ Designed. Curated. Peaceful.
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

10. Serene 2-bedroom cabin with Hot Tub, Deck, &BBQ

Serene 2-bedroom cabin with Hot Tub, Deck, &BBQ
Forestville
$327 nightly
The price is $365
Nov 12 - Nov 13
Total with taxes and fees
Serene 2-bedroom cabin with Hot Tub, Deck, &BBQ
A spacious kitchen with a large island, wooden ceiling, and large windows offering a view of the deck.

11. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
10.0 out of 10, Exceptional, (16 reviews)
"Nice place, great location, had everything we needed. Helpful and prompt communication by the host. This was a great base for exploring the area."
United States
Rebecca I.
$359 nightly
The price is $400
Nov 29 - Nov 30
Total with taxes and fees
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
An outdoor patio with wooden chairs and a table, surrounded by greenery and a white pergola.

12. Peaceful, charming, cottage in wine country. Beautiful yard!

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (14 reviews)
"Great stay and location!"
United States
Brandi K.
$285 nightly
The price is $318
Nov 19 - Nov 20
Total with taxes and fees
Peaceful, charming, cottage in wine country. Beautiful yard!
A room with a brown sofa, two wicker chairs, a small table, and a lamp.

13. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
4.0 out of 10, (1 review)
"Old but quaint. No amenities, no updates. Coffee cups looked like thrift shop purchases. Bed was comfortable. Bath shower drained poorly. Too expensive for a 2 star property."
United States
Chris
$225 nightly
The price is $259
Nov 10 - Nov 11
Total with taxes and fees
Hideaway Cottages
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

14. Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
$461 nightly
The price is $523
Nov 22 - Nov 23
Total with taxes and fees
Russian River Brew-cation Home
A swimming pool with a slide, a barbecue area, and a wooden deck.

15. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (32 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
$231 nightly
The price is $262
Nov 16 - Nov 17
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit
A spacious living room with a wooden ceiling, large windows, and a sectional sofa.

16. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Forestville
10.0 out of 10, Exceptional, (11 reviews)
"Loved our stay. Well stocked kitchen and close to some great little wineries."
United States
Ellen B.
$451 nightly
The price is $511
Nov 10 - Nov 11
Total with taxes and fees
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
A wooden interior with a dining area, a bench, and a mirror on the wall.

17. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (30 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
$398 nightly
The price is $451
Nov 10 - Nov 11
Total with taxes and fees
Cozy Riverfront Cabin - Beach Access & Wood Stove
A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

18. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.0 out of 10, Wonderful, (10 reviews)
"Enjoyed my stay"
United States
Epeli
$79 nightly
The price is $90
Nov 10 - Nov 11
Total with taxes and fees
The Ranch at Lake Sonoma
A dining area with a long table and chairs, large windows, and a hanging light fixture.

19. Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (33 reviews)
"Great place, would stay again!"
United States
Rachel S.
$473 nightly
The price is $527
Nov 10 - Nov 11
Total with taxes and fees
Wine Country Getaway
A patio area with a stone floor, outdoor seating, and a house in the background.

20. Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.4 out of 10, Exceptional, (8 reviews)
"Beautiful place. Bed was extremely comfortable. Overall environment was pleasant. Coffee set up was good for me as a black coffee drinker. We would stay again and would happily recommend it to others."
United States
Brad
$211 nightly
The price is $226
Nov 16 - Nov 17
Total with taxes and fees
Sebastopol Lux Walk toTown Guest Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

DoubleTree by Hilton Sonoma - Wine Country

DoubleTree by Hilton Sonoma - Wine Country

8/10 Good
"Hotels.com’s website did not mention the parking fee. A heads up would have been appreciated…"
Ada 1-night trip
Posted 3 hours ago
DoubleTree by Hilton Sonoma - Wine Country

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $90 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Powell's Sweet Shoppe - Windsor, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Windsor has a good selection of top-notch restaurants and wineries. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that Windsor has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: Visitors like this Windsor vacation home rental. It is located on the waterfront and has a balcony, a selection of books, and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Windsor?

Choose from 30 Expedia vacation rentals in Windsor for a memorable vacation.

What can I see and do in Windsor?

Cultural attractions include Pacific Coast Air Museum, whereas Russian River is a spot to enjoy nature. Windsor Golf Club and Windsor Oaks Vineyards are other places to visit while you're in town.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.